Prof. Laurel Schafer (@laurelschafer.bsky.social)

Congrats to Max Thompson and team, who show that highly functionalized small molecules can be assembled using hydroaminoalkylation. Insights into catalyst and substrate control. A lesson in patience and persistence - his 1st paper, a 1st author JACS!! 🔥🔥 pubs.acs.org/doi/10.1021/...

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Regioselective Hydroaminoalkylation with Silylated Alkenes for β-Amino Acid Synthesis Catalyst and substrate steric and electronic features that influence regioselectivity in hydroaminoalkylation were leveraged to develop a synthetic approach for the selective synthesis of β-amino acids. An in situ generated tantalum-ureate catalyst was used to prepare 18 γ-silylated amines in up to 93% yield from internal silylated alkenes. β-Amino silane regioisomer production was rarely observed, making this work one of the few examples of highly regioselective hydroaminoalkylation with unsymmetric internal alkenes. These γ-amino silanes were converted to γ-amino alcohols with a modified Tamao–Fleming oxidation strategy followed by two additional steps to prepare β-amino acids, including a key fragment of the anticancer drug candidate Ipatasertib. https://pubs.acs.org/doi/10.1021/jacs.4c18706